I have no regret buying V1 Bossk exclusive, mostly because at $150 he was a good value. With this new version being $60 more, I wouldn't get this new one anyways. These $200+ price tags for figures is making me cut way back on purchases. Right now the only figure I'm thinking of getting that's out now or been previewed is the HT Snowtrooper commander to go with my SS regular.
V.1 Bossk was $160 and the new Bossk comes with free shipping (I guess a $15-20 value these days to most US locations) so it's probably closer to a $30 difference, but I hear ya. I despise the prices Sideshow now charges, for figures that are often inaccurate or poorly executed and therefore easily trumped by a new figure (look at SSC DX Vader helmet, SSC Biker Scout helmet, Hoth fig and Luke X headsculpts etc.) People on here constantly try to defend it, but for prices to pretty much quadruple in ten years is $#@%^&! outrageous and openly hostile/insulting to longtime customers.